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US 8,524,738 B2Granted
Quinolinones and quinoxalinones as antibacterial composition
AssigneesToyama Chemical Co., Ltd., Taisho Pharmaceutical Co., Ltd.
InventorsTaro Kiyoto, Tadashi Tanaka, Yasuhiro Tsutsui, Junichi Ando, Mai Motono, Yasuko Kawaguchi, Toshiya Noguchi, Yasunobu Ushiki, Fumihito Ushiyama, Hiroki Urabe
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Abstract
A nitrogen-containing heterocyclic compound or pharmaceutically acceptable salt thereof represented by the general formula: which have a potent antibacterial activity and a high safety. Thus, the compounds are useful as antibacterial agents against gram-positive bacteria, gram-negative bacteria and drug resistant bacteria.
Claims9
A compound represented by formula (I):
- wherein:
- a dashed line represents a double bond;
- R1, R2, R3, R4 and R5 are the same or different and represent a hydrogen atom, a halogen atom, a hydroxy group, a nitro group, a formyl group, an amino group which may be protected or substituted, a lower alkyl, cycloalkyl, aryl, lower alkoxy, cycloalkyloxy, aralkyloxy, alkanoyl, ureido or monocyclic heterocyclic group which may be substituted, -Q1-CONR7R8, -Q1-CO2R9, or -Q1-CN,
- wherein R7 and R8 are the same or different and represent a hydrogen atom, a lower alkyl, cycloalkyl, aralkyl, aryl, lower alkoxy, alkanesulfonyl or monocyclic heterocyclic group which may be substituted, or R7 and R8, together with the nitrogen atom to which they are attached, represent a cyclic amino group which may be substituted;
- R9 represents a hydrogen atom or a carboxy protective group;
- and
- Q1 represents a lower alkylene or lower alkenylene group which may be substituted, a lower oxyalkylene group which is attached to the ring via a terminal oxygen atom and which may be substituted or a bond;
- R6 represents a lower alkyl, aryl, monocyclic heterocyclic, bicyclic heterocyclic or tricyclic heterocyclic group which may be substituted;
- X1 represents a lower alkylene group which may be substituted with one or more groups selected from a hydroxy and a carboxy groups which may be protected, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxy group and an aryl group;
- X2 represents a lower alkylene, lower alkenylene or lower alkynylene group which may be substituted;
- X3 represents an oxygen atom, a sulfur atom, a sulfinyl group, a sulfonyl group, NR10, wherein R10 represents a hydrogen atom, a lower alkyl or lower alkynyl group which may be substituted or an imino protective group or a bond;
- Y1 represents formula
- wherein:
- R11b and R24b are the same or different and represent a hydrogen atom, a halogen atom, a hydroxy group, an amino, lower alkyl or lower alkoxy group which may be substituted, -Q2-CONR14R15, -Q2-CO2R16, -Q2-CN,
- wherein R14 and R15 are the same or different and represent a hydrogen atom, a lower alkyl, cycloalkyl, aralkyl, aryl, lower alkoxy, alkanesulfonyl or monocyclic heterocyclic group which may be substituted, or R14 and R15, together with the nitrogen atom to which they are attached, represent a cyclic amino group which may be substituted;
- R16 represents a hydrogen atom or a carboxy protective group;
- and
- Q2 represents a lower alkylene or lower alkenylene group which may be substituted, a lower oxyalkylene group which is attached to the ring via a terminal oxygen atom and which may be substituted or a bond;
- and
- R12 represents a hydrogen atom, a lower alkyl or lower alkynyl group which may be substituted or an imino protective group;
- R13a represents -Q3a-CONR17aR18a or -Q3a-CO2R19,
- wherein R17a and R18a are the same or different and represent a hydrogen atom, a lower alkyl, cycloalkyl, aralkyl or aryl group which may be substituted, or R17a and R18a, together with the nitrogen atom to which they are attached, represent a cyclic amino group which may be substituted;
- R19 represents a hydrogen atom or a carboxy protective group;
- and
- Q3a represents a lower alkylene or lower alkenylene group which may be substituted or a bond;
- Z1 represents CR20,
- wherein R20 represents -Q4-CONR21R22,
- wherein R21 and R22 are the same or different and represent a hydrogen atom, a lower alkyl, cycloalkyl, aralkyl, aryl, lower alkoxy, alkanesulfonyl or monocyclic heterocyclic group which may be substituted, or R21 and R22, together with the nitrogen atom to which they are attached, represent a cyclic amino group which may be substituted;
- and
- Q4 represents a lower alkylene or lower alkenylene group which may be substituted, a lower oxyalkylene group which is attached to the ring via a terminal oxygen atom and which may be substituted or a bond,
- or a pharmaceutically acceptable salt thereof;
- wherein the substituent group for a lower alkyl, cycloalkyl, aryl, lower alkoxy, cycloalkyloxy, aralkyloxy, alkanoyl, ureido and monocyclic heterocyclic group in R1, R2, R3, R4, R5 and R20 is one or more groups selected from
- a halogen atom,
- a hydroxy and carboxy group which may be protected,
- a lower alkyl, lower alkenyl, lower alkynyl and lower alkoxy group which may be substituted with a halogen atom,
- a hydroxyimino group,
- a lower alkyl, lower alkenyl and lower alkynyl group which may be substituted with an aryl group,
- an aryl group, and
- a monocyclic heterocyclic group;
- the substituent group for an amino group in R1, R2, R3, R4, R5, and R20, is one or more groups selected from
- a lower alkyl, lower alkenyl, lower alkynyl, acyl, alkyloxycarbonyl, aryl and monocyclic heterocyclic group which may be substituted with a halogen atom;
- the substituent group for a lower alkyl group, an aryl group, a monocyclic heterocyclic group, a bicyclic heterocyclic group and a tricyclic heterocyclic group in R6 is one or more groups selected from
- a halogen atom,
- a hydroxy and carboxy group which may be protected,
- a lower alkyl, lower alkenyl, lower alkynyl and lower alkoxy group which may be substituted with a halogen atom,
- an alkylthio group,
- an amino group,
- a lower alkylamino group,
- an acyl group,
- an aryl group,
- a monocyclic heterocyclic group,
- and an oxo group;
- the substituent group for a lower alkyl, cycloalkyl, aralkyl, aryl, lower alkoxy, alkanesulfonyl and monocyclic heterocyclic group in R7, R8, R14, R15, R21 and R22 is one or more groups selected from
- a halogen atom,
- a hydroxy and carboxy group which may be protected,
- lower alkyl, lower alkenyl, lower alkynyl and lower alkoxy group which may be substituted with a halogen atom,
- an aryl group, and
- a monocyclic heterocyclic group;
- the substituent group for a cyclic amino group which is formed by R7 and R8, R14 and R15, as well as R21 and R22, together with the nitrogen atom to which they are attached, is one or more groups selected from
- a halogen atom,
- a hydroxy and carboxy group which may be protected,
- a lower alkyl, lower alkenyl, lower alkynyl and lower alkoxy group which may be substituted with a halogen atom,
- an acyl group,
- an amino group,
- a lower alkylamino group,
- an alkylthio group,
- an aryl group,
- a monocyclic heterocyclic group, and
- an oxo group;
- the substituent group for a lower alkyl group and a lower alkynyl group in R10 and R12 is one or more groups selected from
- a halogen atom,
- a hydroxy and carboxy group which may be protected,
- a lower alkyl, lower alkenyl, lower alkynyl and lower alkoxy group which may be substituted with a halogen atom,
- an aryl group,
- a monocyclic heterocyclic group, and
- an oxo group;
- the substituent group for a lower alkylene group, a lower alkenylene group, and a lower oxyalkylene group which is attached to the ring via a terminal oxygen atom in Q1, Q2, and Q4 is one or more groups selected from
- an oxo group,
- a hydroxy and carboxy group which may be protected,
- a lower alkyl group,
- a lower alkenyl group,
- a lower alkynyl group,
- a lower alkoxy group, and
- an aryl group;
- the substituent group for a lower alkylene group, a lower alkenylene group and a lower alkynylene group in X2 is one or more groups selected from
- a hydroxy and a carboxy groups which may be protected,
- a lower alkyl, lower alkenyl, lower alkynyl and lower alkoxy group which may be substituted with a halogen atom,
- an aryl group, and
- an oxo group;
- the substituent group for an amino group in R11b and R24b is one or more groups selected from
- a lower alkyl, lower alkenyl, lower alkynyl, acyl, alkyloxycarbonyl, aryl and monocyclic heterocyclic group which may be substituted with a halogen atom;
- the substituent group for a lower alkyl, cycloalkyl, aralkyl and aryl group in R17a and R18a is one or more groups selected from
- a halogen atom,
- a hydroxy and carboxy group which may be protected,
- lower alkyl, lower alkenyl, lower alkynyl and lower alkoxy group which may be substituted with a halogen atom,
- an aryl group, and
- a monocyclic heterocyclic group;
- the substituent group for a cyclic amino group which is formed by R17a and R18a, together with the nitrogen atom to which they are attached, is one or more groups selected from
- a halogen atom,
- a hydroxy and carboxy group which may be protected,
- a lower alkyl, lower alkenyl, lower alkynyl and lower alkoxy group which may be substituted with a halogen atom,
- an acyl group,
- an amino group,
- a lower alkylamino group,
- an alkylthio group,
- an aryl group,
- a monocyclic heterocyclic group, and
- an oxo group;
- the substituent group for a lower alkyl group and a lower alkoxy group in R11b and R24b is one or more groups selected from
- a halogen atom,
- a hydroxy and carboxy group which may be protected,
- a lower alkoxy group which may be substituted with a halogen atom,
- an aryl group, and
- a monocyclic heterocyclic group;
- the substituent group for a lower alkylene group and a lower alkenylene group in Q3a is one or more groups selected from
- an oxo group,
- a hydroxy and carboxy group which may be protected,
- a lower alkyl group,
- a lower alkenyl group, a lower alkynyl group,
- a lower alkoxy group, and
- an aryl group.
118 more elements
Dependencies are inferred from the claim text.